Pure Sin
by Sweet Scarlett Angel
Summary: AU/AH. Elena Gilbert was a good girl. A shy girl. A smart senior counting off the days until graduation and hoping to get into the college of her dreams. Enter Damon Salvatore a popular senior willing to do anything to date the homecoming queen, including pretending to be in love with Elena Gilbert. Delena.
1. Good Girl

**Prologue: Good Girl**

"_Yeah, but he never takes em' serious."_

"_Ah, but someday he is meeting someone different. Some delicate, fragile creature who's giving him a wish to shelter and protect."_

"_Like Miss Park Avenue 'ere, eh, matey?"_

_-The Lady and the Tramp (1955)_

* * *

><p>Elena Gilbert was a good girl.<p>

There was honestly no other way to describe her. She didn't lie or steal or swear. She didn't smoke, or drink. She didn't ditch classes or go out partying every night. She was truly a good girl.

Elena Gilbert was an only child living in a secluded town by the name of Mystic Falls in the middle of nowhere in Virginia. It was the kind of town where everyone knew everyone, where the biggest problem were a bunch of teenagers smoking weed and drinking behind the tombs in the local cemetery.

In short it was the picture perfect town, the kind where musical movies were based on and where everyone would have liked to live. Except Elena. Elena hated Mystic Falls with a passion.

The small town just felt too crowded, it felt like everyone was constantly in her business and she had known these people since the minute that she was born. Elena wanted to stretch her wings and fly towards the real world. The kind of world in where people her age didn't wait for the weekend to do jello shots and get naked in somebody's hot tub.

Elena wanted to have an actual, intelligent conversation, in short she wanted to leave this sad, little town. The problem was that no one seemed to understand that, not her father not her best and only best friend Bonnie Bennett.

And while they might be content to live in this little town, Elena was not. She would get out of here the first chance that she had. More specifically Elena had a plan she would finish her last few horrible months of high school, work one last summer at Rose's diner, pack her bags in her new car and drive to her new school and home which was Yale.

Well, she had to get in first, but thankfully her acceptance letter (hopefully) was only a few months away.

Elena lived alone with her father in a two story house that seemed far too big for just the two of them, especially since her father spended more time at work than at home and Elena was usually at cheerleading practice, working at the diner, or at the library trying to keep her grades up.

Her mother, Miranda had died when Elena was six in a fatal car crash, Elena didn't remember her much since she had been too little, but she did remember her mom's younger sister, Aunt Jenna coming to live with them for a few months and her father almost always being sad all the time. Not exactly pleasant memories.

Elena's father was Dr. Grayson Gilbert, a cold, strict man and head of the surgical ward at Mystic Falls Hospital. But all though Grayson could be strict at times it was obvious that he loved his daughter, even though sometimes he could be too overprotective.

But then again he didn't have to worry about Elena much. Elena was a good girl.

And nothing bad ever happens to good girls.

Unless they stumbled across a bad boy on the way.

-End of Chapter One-

Please review! I know this chapter was kind of short, but it's just the intro, I promise that the next one will be longer!


	2. Miss Independent

**Miss Independent**

Elena Gilbert sighed as she watched the pink flamingo clock that was hanging in the buttery yellow walls of Rose's Diner, the diner that she had been working at for the past two years ever since she was sophomore. Elena ignore the beady yellow eyes of the bird and instead focused on the hands of the clock: 6:39 PM.

She gave another sigh, she still had a couple of hours to go, the diner closed at ten and she promised Rose that she would close the diner herself at ten, even though her legs and back were throbbing from exhaustion thanks to the cheerleading practice that they had today, but she couldn't very well refused since Rose had been worried enough with her seven years old twins both sick with the flu and Elena had felt pity for her and had offered to close the diner for her.

Elena tried to ignore the fact that she had about two hours of homework to get through that mostly consisted of Calculus and AP Biology. Fun. She looked at the I Love Lucy calendar that Rose had plastered on the wall. January 31st.

Five long months until graduation and only two until she found out if she did get into Yale. She hoped that she did, she had to get into Yale, and she supposed that Whitmore College or the University of Virginia wouldn't be that bad, but she wanted to leave Virginia, just the thought of staying in Virginia for another four years gave her the hives.

"Order up," Luke Parker one of the youngest chefs working at the diner gave her a quick smile as he placed a plate filled with a turkey sandwich and fries and another one with fried chicken and coleslaw.

Elena smiled at him. "Thanks, Luke." She grabbed the plates and walked towards the back of the diner where little old Mr. and Mrs. Louise were waiting for their dinner. "Here you go," Elena said with a smile as she placed down the plates. She briefly caught a reflection of herself.

One of the things that she hated the most about working at the diner was the stupid uniform. It consisted of a cap sleeve dress in the worst shade of green imaginable and a frilly white apron, the one that reminded her of the little apron that Alice used to wear in Alice in Wonderland.

"Thank you, sweetheart." Mrs. Louise said, Mr. Louise didn't say anything and just continued to eat his food.

"No problem," she tugged back a piece of dark hair that had come loose form her ponytail. "Do you need anything else?"

"No, thank you, Emma we're fine."

Elena nodded as she returned back to the kitchen, ignoring the fact that Mrs. Louise had called her the wrong name, the Louises were pushing eighty and came for dinner every Friday night. Elena remember that for a long time Mrs. Louise had called her Amara, at least Emma was a lot closer to her name.

"Hey," she gave a soft smile to her best friend and co coworker Bonnie as she took a sip of water. At least the uniform look better on her and it matched her pretty green eyes.

"Hey," Bonnie chuckled. "So did Mrs. Louise give you another name this time?"

"Yes, Emma." Elena rolled her eyes as she looked at the diner, it was empty tonight just a few older couples having dinner. Elena noticed with a pang of regret that she would be the only one here tonight after Bonnie's shift finished at 7:30 and to be honest that freaked her out a bit. "At least this time it's closer to my name."

Bonnie snorted. "At least she doesn't call you Benny or Betty, and she actually smiles at you, the old geezer hates me."

Elena stopped mid laugh when the door opened again as new customers started arriving. Bonnie noticed her expression. "What-oh, them."

The them that Bonnie was talking about consisted of the most popular girl and queen bee at Mystic Falls high school, Rebekah Mikaelson. Rebekah was tall, beautiful, confident, and with a sharp tongue and a slight British accent since she had lived in Europe for a time, following behind her when her usual group which consisted on Caroline Forbes, Matt Donovan, Tyler Lockwood, and a few other people that Elena didn't recognize her.

To say that Elena didn't like Rebekah was an understatement, Elena hated the girl and with good reason, she had been making Elena's life miserable since freshman year always making a snarky comment which annoyed her since Elena had never done anything to Rebekah, but she was easy to pick on.

Bonnie gave her a sympathetic look. "Want me to take it?"

Elena shook her head as she grabbed her notepad and pen. "No, my side, I'll take it." She headed towards the crowded table trying to keep her cheeks from heating up like they always did when she grew embarrassed. "Hi guys," she said. "What can I get you?"

"Just water for me," Rebekah said crisply, wrinkling her nose at Elena's uniform. "There's nothing here I can eat, don't want to be fat for prom."

"Oh, please you're so skinny." Caroline Forbes chirped. Caroline was a junior and followed Rebekah around with hero liked adoration she was like a cute, clueless puppy dog. "You can eat anything and not gain an ounce."

Rebekah stood up a little straighter. "I know."

"I'll have the burger with fries and a large coke." Tyler told her without bothering to look up from his phone.

"Ribs with Cole slaw." Matt said as Elena scribbled down the rest of the orders.

"Anything else?"

"No," Rebekah said sharply. "Now hurry, I'm practically dying of thirst."

Elena fought the urge to roll her eyes as she went back to the kitchen and handed the order to Luke. Elena was just filling a glass with water when she heard the door open again. She turned around and saw that this time the one who had come in was Damon Salvatore.

There was no doubt in anyone's mind that Damon Salvatore was handsome, perhaps not in a movie star kind of way, but he had that bad boy image that made all of the girls swoon over him, though Elena didn't know why.

Elena had only shared a few conversations with him (the longest one being 'can I borrow a pencil?) and honestly Elena didn't know what all the fuss was about. Yes, he was handsome that was for sure, with his velvety dark hair and icy blue eyes, but other than that he was an arrogant, selfish, prick.

Swinging his hips slightly he sat down next to Rebekah and put his arm around her kissing her on the cheek, making her giggle.

"You better get that water on the table," Bonnie pulled her out of her thoughts. "Before Rebekah has a seizure."

Elena nodded as she sucked in her cheeks and went towards the table.

* * *

><p>Damon looked across the nearly empty diner trying to look for Rebekah Mikaelson, the only reason for being in this dingy little diner, he had no idea what Rebekah liked about this place, but Damon was prepared to go to Rome if it meant that he got to spent time with her.<p>

Rebekah was easily the most popular and prettiest girl in school with their matching blue eyes and her pale gold hair and the homecoming queen crown being always invincibly on top of her head. Damon had always been smitten with her, and all though Rebekah had flirted back, she had never attempted to make the first move and that irritated Damon as well as enchant him, he loved a good chasing game.

"Yo, Salvatore over here!" Tyler cried out from the booth where everyone seemed to be squeezed at. Damon ignored Caroline his new stepsister. The previous summer his father Giuseppe and Caroline's mother, Sherriff Liz Forbes had gotten married and Damon and Stefan had gotten a stepsister.

Secretly Damon wondered what Liz saw in his strict, no nonsense father, the man could practically put fish to sleep and he liked Liz, at least Liz was cool and had a personality.

He squeezed in between Matt and Rebekah and wrapped an arm around Rebekah and kissed her on the cheek. "Evening gorgeous."

"Evening." Rebekah said coolly as she took a sip of her water. "You're late."

"Why did you miss me?"

"You wish."

He turned slightly and saw the mousy, brown hair girl that sat next to him in English carrying platefuls of food, what was her name Cindy, Ella, he honestly couldn't remember. She turned to him. "Would you like something?"

"Cheeseburger," Damon said without bothering to look up. "And a coke."

The girl took his order and scurried off.

Rebekah stood up and grabbed her handbag. "Well, while you boys are eating like pigs I think I'll go freshen up. Coming Caroline?"

Once the girls had left Matt punched Damon on the shoulder. "What the hell man? I was totally winning her over."

"Oh, please Donovan." Tyler sneered. "You were too busy drooling over her."

"Even so," Matt frowned. "You shouldn't butt in."

Damon rolled his eyes as he stole one of his fries. "Oh, stop being such a pussy, Matt. I didn't ruin anything sexy Becks is a prize to be won, if you can't handle it leave the race."

"Oh I can handle it," Matt narrowed his eyes as Elena placed Damon's food on the table and scurried off. Matt looked at Elena before he turned to Damon. "Hey, are you in a mood for a bet?"

"Always."

"You know Elena right?" Matt asked him. Elena was collecting dirty plates from another table.

"Briefly. So."

Matt smirked. "I'll make you a deal, if you can make prissy Elena Gilbert fall in love with you in let's say in fourth months by May 2nd, Prom Night. I won't come back after Rebekah she'll be all yours."

"Really? It might make things move a little bit faster without you slobbering all over the place."

"So what do you say?"

Damon looked at Elena, small, plain, probably low self-esteem. Should be a piece of cake. "Donovan, you have yourself a deal."

-End of Chapter Two-


	3. Bad Boy

**Bad Boy**

"Thank you," Elena said tiredly once the last customer left the diner at half past ten. "Come again." She closed the door behind them and sighed, finally alone. Thankfully, there wasn't too much of a mess and the waitresses of the moaning shift will take care of it.

She hurriedly swiped the floors and cleaned the counters and tables, she made sure that everything was off and then grabbed the big iron key sets that Rose used to lock the diner and closed it. She tightened her cardigan around her thin frame and grabbed her bag tightly, she hated walking alone at night, and she needed to learn how to drive. She was practically the only senior who couldn't. Talk about embarrassing.

She gave the door one last pull to make sure that it was fully locked. She turned around and nearly ran into Damon. She gave a small jump back and Damon gave her his famous smirk. "Scaredy cat."

Elena scowled at him. "I am not a scaredy cat and you shouldn't jump out of nowhere."

"It's that against the law, Miss Gilbert. I thought my stepmother was the sheriff."

Elena could feel her temper rising, but she wanted to control herself. This is what Damon did, he liked pushing people to their edge and she was not giving him the satisfaction. She walked across from him. "Goodbye, Damon."

"You know my name." Damon said sounding surprise.

"It's not that amazing," Elena's tone was oozing with sarcasm. "We have been in the same class since first grade."

Damon blinked once, then twice. Had they? Damon vividly remembered a young, dark hair girl always preferring to draw instead of playing tag with the rest of them. "I, uh of course. You changed. I didn't recognize you."

"I haven't change at all," Elena pointed out. "We're in the same English class."

Damon could feel his own ears reddened despite himself, Elena was really calling all the shots and he was screwing up. He cleared his throat and pretended that he hadn't heard the comment. "Would you like a ride?" he was gazing to his shiny, pale blue 1969 Chevy Camaro. He had worked for hours at an automobile repair shop to earn the money and while his father detested the car, Damon loved it. It was his baby and it was a classic.

Elena shook her head. "I don't live far from here, I can walk."

Damon frowned. So this wasn't going to be that easy. "It's late though, there are probably buglers out there . . . and serial killers and vampires you never know."

Elena snorted. "Serial killers and vampires in Mystic Falls, really?"

"Good point," he didn't want to beg, he really didn't want too, but he could see that Elena was too stubborn to take a hint. "Come on, let me be a gentleman and give you a ride."

Elena pushed back a piece of hair from her face. Damon a gentleman that was a laugh, but it also confused Elena. Damon had been ignoring her for the past ten years why was he suddenly being so friendly. Elena had a feeling that he wasn't going to give up, so she took a deep breath. "Ok, fine. Thanks for the ride."

Damon hid back a winning smile and Elena got inside the passenger seat. "What's your address, doll?"

Elena ignored the flirtation. "2101 Maple Street. It's the house with the brown roof and the green shutters." Damon nodded as he drove out of the driveway. An uncomfortable silence had settled in the car and Damon turned on the radio.

Elena looked a little surprise. "You like Elvis?"

"All the classics." He gave her a sly smile. "You?"

Elena nodded, smiling slightly. "My father collects vintage records of him-Dr. Grayson Gilbert he works at the hospital."

Damon nodded as he parked the car in front of her house, she could see that her dad had already arrived. "Home sweet home and safe and sound."

"With no vampire in sight." She turned to him and gave him a sincere smile. "Thank you for the ride, Damon. See you at school on Monday."

Damon nodded. "See you."

Without looking back Elena hopped towards home and closed the door behind her, she saw that the lights were turned on and was surprise that her father wasn't asleep yet. Grayson usually slept early because he had to get up early the following morning. "Daddy?"

"In the kitchen," Grayson called out, he was drying his hands together and the air smelled like burnt pasta. Even though Miranda had been gone for eleven years now her father still had no idea how to cook, they ordered take out most of the time, but neither him nor Elena were good cooks. "Did you eat anything, why are you so late?"

"Sorry, Rose's twins got sick I needed to close the diner," Elena said tiredly. "And I ate something at the diner." She doubted that a couple of cookies counted for an actual dinner, but Elena was too tired to eat anything.

"Who drove you home?" Grayson asked with a pointed gaze. "It wasn't Bonnie."

"No," Elena replied, there was no point in lying to him. "It was Damon, he goes to my school."

Grayson frowned. "Giuseppe's kid? He's a troublemaker, I hope he wasn't giving you too much trouble."

Elena scoffed. "Hardly, he was just driving me home. We barely talk. Good night."

"Night," Grayson said. "Oh, just so you know I'm working a double shift tomorrow, are you ok with getting dinner?"

Elena nodded, she knew the routine and thanks to her dad working all the time she managed to be independent. She closed her bedroom door and peeled off her clothes and settled into her comfortable winter pajamas and then did what she always did every night. She wrote in her diary.

She flipped through the pages until she finally found a clean page and pause. "Dear Diary," she paused, what would she write. "Damon Salvatore gave me a ride today, which was weird, but not at all unpleasant. . ."

* * *

><p>"I'm telling you Donovan I had her eating from the palm of my hand." Damon was parked in the garage at the Salvatore house with his phone pressed to his ear. "Girls like Elena Gilbert are easy to play with a wink and a ride on this car and they are on cloud nine, I'm going to win this bet sooner than graduation."<p>

"You're a dick," Matt spat and Damon was pleased at his annoyance.

"Jealousy is not pretty on anyone Donovan, especially not on a baby face like yourself. Accept defeat and we can call it a day."

"Nice try A-hole, but until I see goody two shoes Elena Gilbert weeping at your feet, you aren't getting shit."

"Damon? Is that you? Are you out there?" a stern voice said.

Damon held in a groan. "Go to go, Sergeant Jackass sounds pissed."

"Is he ever not?" Matt laughed.

"Good point." Damon said as he turned off his phone and exiting his car, his father Giuseppe had spent most of his life in the military, though he seemed to believe that everything around him was an army base, talk about annoying.

"Where have you've been?" he asked suspiciously. "It's late, your curfew is at ten, what have you've been up too," he grasped his arm. "Talk Damon."

"Dad, it's Friday," Stefan, his younger brother by one year AKA the favorite son tried to speak up in Damon's defense, something that was rare, but when he did, he did it with a good heart. "Does it matter if he was-"

Giuseppe gave him the evil eye. "Yes, it matters, Stefan what will the neighbors think?"

Damon fought the urge to roll his eyes. That was another thing that annoyed him about his father. He really cared about what other people said about him. "I was giving Elena Gilbert a ride, she didn't have a car. It was late."

Giuseppe perked up slightly. "Elena Gilbert? Dr. Grayson Gilbert's daughter, the sweet girl?"

"Um, yeah that's her."

His faced softened a little. "I like Grayson, he's a good man and I'm beyond relieved that you're hanging out with nice girls for a chance, though call next time."

"I will." He didn't hear the sarcasm in Damon's voice. He turned to Stefan who was giving him a puzzle expression. "What?"

"Nothing." He said.

Damon walked towards his room and ran into his stepsister Caroline whose hair was in curlers and she was wearing a fluffy pink bathrobe. Damn, he still wasn't used to having girls around. "What?"

"Nothing," she said. She was still a little shy, even though they lived in the same house together. "I just think that it's very nice that you're giving Elena a ride, not many people would. She's always nice to me, when I go to the diner. I just thought that I should let you know."

"I'm always nice," Damon argued, trying to ignore the tiny lump of guilt forming. "Good night."

-End of Chapter Three-

Thanks for your reviews!


	4. Wrong Side

**Wrong Side**

"Damon Salvatore gave you a ride?" Bonnie arched an eyebrow the following Monday as she parked her car in front of the school. She turned and faced Elena who wasn't smiling or anything, it was like Elena had been talking about what she had for breakfast that morning. "And you accepted?"

"I tried to decline," Elena pointed out as she got out of the car. "But it was late, and you know how much it freaks me out to go alone at night. Besides you know how stubborn he can be, it was just easier to go along with it."

Bonnie still didn't look convince. "And he didn't try anything? No rude remarks, no sarcastic phrases?"

Elena let out a small laugh as she tightened her grip on her bag, which felt slightly heavy thanks to her uniform. Normally, Elena in a million years would never try out for cheerleading, but her mother had taken her to gymnastic classes a lot when she was little and Bonnie had practically forced her to try and she had made the team.

Elena didn't dislike it, but it wasn't her favorite activity she had to admit, but it was well enough for her college applications and most of the girls on the teams were nice, besides as long as she got her kicks and cartwheels right, they would mostly leave her alone.

"Bonnie, he's our classmates, not a serial killer." Elena laughed as she paused in front of her locker and started taking out her history book.

Bonnie gave a shrug. "I'm just telling you to be careful, this is Damon that we're talking about. He thinks that torturing people should be an Olympic sport."

Elena snorted. "Calm down Detective Bennett."

"Speak of the devil and he will appear." Bonnie murmured slightly causing Elena to be surprise. She turned towards the direction that Bonnie was looking at and saw that Damon was coming over here.

He pressed a hand on her locker shutting it close and giving them his trademark smirk. "Bon Bon. Elena."

"Bonnie," Bonnie corrected slightly annoyed. "I'll see you in class." With one last be careful look to Elena, she left leaving Damon and Elena alone.

"She doesn't like me much." He stated.

"No, she," Elena hesitated, not really sure what to say. "Well, it's safe to say that you get on her last nerve."

"Ouch." He winced. "Lucky me, so how was your weekend?"

"Ok." Elena murmured as she looked into her locker, slightly distracted, where had she left her history notes? "Did a little shopping, laundry the usual."

"Yeah." Damon cocked his head slightly noticing that Elena seemed more interested in the locker than in him. "So listen, are you busy next weekend."

"I don't think so," Elena smiled in relief when she finally fished out her history notes that had been squished in her math textbook. "Why?"

"Because if you don't have plans I was wondering if you would like to go out?" he said, wiggling his eyebrows slightly.

"With who?" Elena asked slightly confused and staring inside her locker again.

"With me," Damon said losing his charm for a minute. Was she really that naïve or was she playing with him? "I'm asking you on a date, Elena."

"Oh," Elena stumbled for a bit with her papers and some blush settled on her cheeks. "I didn't realize, I mean I hadn't expected-can I think about it?" she finally managed to ask.

"Of course," Damon said looking rather proud of his accomplishments. "Take all of the time that you need."

* * *

><p>Elena knew that it was beyond vain, but Damon's words kept ringing in her ears and she seemed to be in a daze in wherever class she went. In math she could hardly solve her equations and in English she could swear that Damon's intense blue eyes were staring back at her.<p>

Her history teacher, Mr. Tanner had, had to ask her twice who the thirteenth president of the United States was before she mumbled an answer.

She hated herself for acting like such a school girl, she was almost an adult, in a few months she would be off to college and here she was worrying about things that fifteen years olds should be worrying about.

At her age she should have already had her first kiss and first date and maybe even her first time, but Elena was always too shy to talk to boys and the boys that she did like never liked her back. Love was a battlefield after all.

But she had never been asked properly on a date before and never in a million years would she have thought that Damon would ask her out, don't do it, a little voice inside her head managed to say, you'll regret it.

But for once Elena ignore the little voice inside her head, what harm could it be to go on one measly date and so she decided to tell her best friend, the only person that should be happy for her, but she doubted it.

"Damon?" Bonnie hissed at her that afternoon during lunch as they washed their hands in the girls' bathroom, thankful that no one else was there. "Damon asked you on a date and you're seriously considering on going?"

"What's the big deal?" Elena couldn't help, but feel annoyed. She understood that Bonnie was concerned, but would it kill her to offer a little support. "It's just one date, we'll go out for pizza and we'll probably never see each other again."

"But are you sure about this?" Bonnie blurted out. "I mean, he has never showed interest until now, why-"

"Thanks, Bonnie," Elena said hotly. "Thanks for the support."

Bonnie appeared to be wounded for a moment. "Oh, Elena you know I didn't mean it like that, I just want you to be careful and of course if you want to go on this date then you should, it's your choice."

Before Elena could reply the double doors opened and Rebekah came in, obviously unhappy and dressed in a pair of super skinny jeans and a red leather jacket. "Bonnie," she gave her a very bitter smile. "Leave, I want to talk to Elena."

A small annoyed look passed over Bonnie's face, but she left the bathroom. Elena started feeling uncomfortable. "Can I help you, is this about cheerleading?"

"You know very well that this is not about cheerleading." Rebekah replied hotly as she looked at her strangely. "I've heard some rumors, I don't know if they are true, though I don't even know why I'm bothering asking you."

Elena raised an eyebrow. "Yes?"

Rebekah finally took a deep breath and blurted out. "Is it true that Damon asked you out? The Damon that went with me to Rose's diner last Friday night?"

"Yes," she admitted and saw that Rebekah looked a little pissed. "Is everything all right?"

Rebekah forced a smile. "Yes, everything is all right, just a word of advice Elena, I know men like Damon and they like to play rough . . . so don't think that everything will be like roses."

"Don't worry, I didn't expect it to be." Elena replied firmly. Honestly, why was everyone acting like Damon and Elena going out was an international crisis? Without another look back, Rebekah left the room and Bonnie came back a minute after.

"Well, what did she want?"

Elena shrugged. "To scare me again, she kept going on and on that Damon wasn't a nice guy and wondering why he would want to go out with me."

"I'm sorry, I was being a bad friend," Bonnie sighed. "If you want to go out with Damon, you should. I won't pretend to be happy, but I will support you."

Elena's face softened. "Yeah, I've been thinking about it and I think I am going to accept. I mean I have to go on my first date someday and who knows maybe it won't be that bad."

"Maybe." Bonnie replied, but she didn't sound entirely convinced.

* * *

><p>"Is it true?" That was the first thing that Caroline asked him the minute that Damon came through the doors later after school, hoping he didn't smell like cigarettes. Like always the house was eerily quiet. Liz usually worked late and Stefan was in his room listening to music and doing his homework.<p>

Damon looked at Caroline, it was hard thinking that Caroline was only a year younger than him. She looked so young. "Is what true?"

"Did you ask Elena Gilbert out?" Caroline chirped.

"How did you-"

"Rebekah told us," Caroline replied. "Anyway good for you she's really nice-"

"Wait," Damon perked up. "What did Rebekah say-"

"What is this Damon, who are you going out with?" Giuseppe came into the room, his eyebrow raised slightly.

"Elena," Damon asked annoyed. "Elena Gilbert, you don't mind, do you."

"No," Giuseppe said surprising him, most of the time he wanted Damon to live like a priest. "Elena is a nice girl. Have a good time."

-End of Chapter Four-


	5. Daddy Dearest

**Daddy Dearest**

She had accepted.

Twenty fours later and Elena still couldn't believe it herself, not that she had been asked out, but that she had accepted to go on a date with the biggest playboy in school, the boy who was trouble, sass back to all the teachers, and worship the ground that Rebekah Mikaelson walked on.

But if he did like Rebekah, then he wouldn't ask her out, Elena chided herself, she needed to stop being so negative. Elena flashed back to yesterday when she had accepted after English class, one of the few classes that she and Damon actually shared.

She had ran up to him, after class slightly pulling on his leather jacket and telling him that she would go out with him. Damon had given her a slight smirk and simply said. "Cool. How about Friday? The fair is in town, I'll pick you up at seven."

Elena had nodded, silently relieved that they weren't going to the usual dinner- movie date at least at the fair there wouldn't be any awkward silences and there was a much lesser chance of running into somebody that they knew. The fair was perfect.

Bonnie being her best friend hadn't uttered a negative peep when Elena told her that she was going to the fair on Friday even though she was dying too and instead just offered to do her makeup and hair. Now there was only one problem, telling her father. Since she had never gone on a date before it wasn't like she had enough practice and she didn't know what Grayson would say, since he was a tad overprotective.

Elena glanced toward her clock on Wednesday night, it read 8:35 PM. Her dad was late, not that was unusual, Grayson usually worked overtime, he wanted everything in the hospital to be perfect. Elena closed her math textbook, ignoring the math sets that she needed to do and instead went towards to her closest and opened it. Now a new problem occurred, what was she going to wear?

It was the fair, so it wasn't like she was going to show up in a dress and heels, but still she wanted to look nice on her date. She started pulling apart her closet, ignoring the boring skinny jeans and t-shirt that she usually wore.

She finally decided on a pair of black skinny jeans, a purple tank top, and matching black booties. She looked at the outfit and nodded, it looked cute and it wasn't too showy, the last thing she needed was for Damon's ego to rise if he thought that Elena was dressing for him.

She finally heard the door close and Elena hurried downstairs. "Hi, Daddy," she squeaked as she gave Grayson a peck on the cheek. Like always her dad smelled like that weird, clean hospital smell, coffee, and Chinese take out.

"Hi, honey," Grayson noticed that Elena was fidgeting slightly. "Is there something that you want to ask me?"

"Actually yes," Elena blurted out. "Can I go out on Friday? The fair is in town."

Grayson nodded as he put his keys on the coffee table. "With Bonnie?"

"No, actually," she chewed her bottom lip, hating that she was so awkward. "With a boy, Damon. Actually, Damon Salvatore."

Grayson looked at her. "Giuseppe's kid, Liz's step-son?"

It took a while for Elena to remember that Damon's dad had married Caroline's mom. "Yeah," she said quickly. "So can I go, to the fair? I promise I will be back before midnight."

Grayson nodded, looking a bit tense. He hadn't really heard good things about Damon, but he had only heard things and it wouldn't be fair to judge a boy only by things that he had heard, besides Elena looked really excited and Grayson couldn't take that away from her. "All right, on one condition."

Elena's smile fell a little. "What's that?"

"I have to meet him first."

* * *

><p>"Elena Gilbert didn't show up, today tragic," Rebekah tried to keep the bitterness out of her voice, but it was far from easy. It was a cloudy February Friday afternoon after school and the cheerleaders in their short shorts and sweatshirts were huddled in the football field silently cursing Rebekah for scheduling practice when it was freezing.<p>

Rebekah didn't fancy being in the cold much either, but she had been hoping to make practice run a little late today so that Elena would be late for her date. Pathetic, she knew but she was running out of options.

She knew that Damon had been following her like a puppy dog forever and he had stopped chasing her to chase after quiet Elena and that had really stung. But Elena hadn't showed up to practice at all. Little Miss Goody-Goody obviously had other plans, that didn't include following her responsibilities to the cheerleading squad.

"Caroline!" Rebekah barked over her shoulder and Caroline came bouncing over to her in a matching red and white cheerleading uniform. "Since you and Damon became stepsiblings, you must um, spend a lot of time with each other."

Caroline frowned, confused. "Not really, I usually spend more time with Stefan-"

"Irrelevant," she interrupted as she pushed back her blond hair into a ponytail. "So do you have any idea what Damon and sweet, innocent Elena are doing tonight?"

Caroline thought for a moment. "They are going to the fair."

Rebekah frowned. "The fair?"

Caroline nodded. "Yeah, the fair is in town, they have a bunch of food, games and stuff-"

"I know what a fair is," she snarled then tried to calm down her temper. "I just thought that they would sneak into a club or got to a concert or something."

Caroline shrugged. "I guess Elena likes things a little different."

* * *

><p>Five minutes to seven on Friday night, Damon exited his car with a smirk on his face. He was dressed in jeans, a white t shirt, and his signature black leather jacket. He rang the doorbell and greeted Elena with a smile. She looked pretty today, slightly darker and Damon liked dark clothes on girls, her soft, dark brown hair was pulled back. "Hi."<p>

"Hi," Damon said. "Ready to go."

Elena mumbled under her breath. "Look, I'm sorry about this, but my dad actually wants to meet you first. It won't take long I promise."

"Me?" Damon sounded a bit startled. "Why would he want to meet with me?"

"Please," Elena said as she opened the door wider and Damon came into the hallway. "He's in the living room."

Damon entered the living room, aware that Elena wasn't following him. He saw a tall, dark hair man sitting on a chair reading the newspaper. "Mr. Gilbert?"

Grayson looked up and gave him a tense smile as he noticed Damon's leather jacket. "Good evening, Damon. You're Giuseppe's oldest son, right? How is your family adjusting since your father got remarried and all?"

Damon nodded, feeling awkward. "We're getting all right, I mean Liz is cool and Caroline sure is . . . something."

Grayson nodded. "So you kids are going to the fair?" when Damon nodded yes, he continued. "I won't take too much of your time, just be aware that I love my daughter very much Mr. Salvatore and all that I'm asking is that you take care of her and respect her, she is my only child."

Damon nodded again feeling like a root. "Duly noted and don't worry Elena is safe with me," Damon turned on his heels and left before he could continue and almost ran into Elena who seemed to have been listening in.

"Sorry about my dad," Elena blushed. "He can be embarrassing and over bearing but he can been sweet once you get to know him" Damon hoped that he and Grayson wouldn't have to interact anytime soon.

"Ready?" Damon cocked an eyebrow and offered his arm.

Elena gave him a nervous smile as she took it. "Ready."

-End of Chapter Five-


	6. Fun at the Fair

**Fun at the Fair**

The annual was already at full swing once Elena and Damon arrived and found that it was filled with people buying food, trying to win games at the game booth, and itching to get on the rides. Elena looked around in amazement, feeling like a little kid. She knew the fair was supposed to bring joy to children, but honestly Elena felt like a child again when she went to the fair and amusement parks.

It reminded her of a happier time, back when both of her parents had been alive and they did fun stuff like that, before she and her father had become so isolated even from each other and before Elena started to wonder if things would ever start to feel normal again after her mother died.

Damon squeezed her arm slightly as he led her towards the ticket counter, reminding Elena that she was not alone, that she wasn't that lonely, sad little girl without her mother. Times had changed and she was on a date and she was determine to have some fun even if it killed her.

After Damon bought the tickets, he turned to her. "Where do you want to go first?"

"The Ferris Wheel," Elena blurted out, it had been her favorite ride when she was a kid.

Damon nodded as he arched his way towards the rollercoaster. Damon preferred the fast rides over the happy go-lucky ones. "Do you mind if we ride the Roller coaster first? It's not as packed, surprisingly and we can go to the Ferris wheel after."

Elena bit her lip as she looked towards the rollercoaster, she could hear the people screaming even from where she was standing. She usually wasn't a fan of the fast rides. She squirmed. "I don't know-"

There was a twinkle in Damon's eyes as he teased her. "Don't tell me you're scared. Scaredy cat."

Elena refused to blush as she raised her chin defiantly. "I am definably not scared, Damon Salvatore, let's do it."

But Elena found herself regretting those words when she found herself buckled up in the front seat of the cart next to Damon as they began moving upward the steep hill, Elena felt like she was going to throw up, oh why had she talked herself into it.

Damon turned slightly and saw that Elena looked like she was about to die. He found her sweaty hand that was curled up into a tight fist and squeezed it. "Close your eyes," he instructed. "It will go faster I promise."

Seeing that there was no room to argue, Elena closed her eyes tightly and buried her head against Damon's leather jacket. She could smell the leather from the jacket and his spicy cologne as he squeezed her hand.

Elena felt a jolt in her belly as she felt the car go down, then up, and to the side until she felt her whole dinner practically dancing inside her belly. She let out a small gasp as the cart finally stopped. She looked up at Damon weakly who was looking at her amused. "Is it over?" even though the cart had stopped moving, Elena had refused to let go off his hand for a second.

Damon let out a small laugh as he helped her up. "It's over. Don't worry, we'll avoid anything fast, so what's next on the list? Ferris Wheel?"

Elena shook her head. "I think I should avoid heights for the future. Let's go play a game instead."

"Your wish is my command." Damon said as they walked towards the game booths were stuffed toys and football t-shirts were hanging by the edge.

"This one." Elena stopped short in front of a booth. The key was to knock down all three of the bottles that were standing in pyramid formation.

"One dollar for three balls, little lady." The man said as Elena handed him a dollar. She grabbed the first ball and threw it, the first one ended hitting the wall, the second one ended up on the floor, and the third one ended up knocking down the doll that had been hanging by the edge.

Damon smirked. "You really suck at this, you know that."

Elena stuck out her tongue. "Like you could do any better."

"I could and I'll show you." Damon smirked at her as he handed the man a dollar and the man handed him three balls. Damon missed the first two and Elena arched an eyebrow as if saying I-told-you. "I'm not done, am I?" with the last ball Damon managed to knock down the three bottles and Elena let out a small gasp.

"Winner!" the man cried out as he handed Damon a stuffed panda bear.

"Here." Damon said handing the bear to Elena.

Elena felt herself blush slightly as she gripped the bear to her chest. "Are you sure?"

Damon snorted. "Elena, believe me I don't need a stuffed bear, besides it can serve as a reminded for you never to underestimate me."

* * *

><p>"Do you want to get some ice cream?" Elena said breaking the silence on the ride back home from the fair, it was only ten-thirty and she still had half an hour before her curfew. They were just about to past Dipper Dan's, the local ice cream parlor. "My treat." After eating soft pretzels and salty popcorn, she craved something sweet.<p>

Damon headed towards the drive though and Elena asked for a vanilla scoop with peanut butter sauce and Damon asked for a scoop of regular chocolate as they headed back home. After a few second Elena let out a small laugh.

"What's so funny?" he asked.

Elena shrugged. "It's just its strange, don't you think? We've been in the same class since we were children and this is the first time we've hang out after school hours."

Damon's hands tightened on the wheel. "I don't think it's that strange."

Elena licked off the peanut butter sauce off the spoon. "Really, you don't think it's even the tiniest bit weird going out with a person who you haven't spoken too since first grade?" Damn, could Elena read minds or something?

Damon laughed, uneasily. "I think you're too paranoid for your own good."

Elena gave a little shrug and she finished her ice cream. "Perhaps you're right, I didn't mean to sound ungrateful, and I think my dad's overprotectiveness is starting to rub off."

"Well, you have nothing to worry about," Damon reassured her as he looked at her. "There is no funny business going on."

-End of Chapter Six-


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